High-Stakes Erotic Match!!!

by Kaneki_Ken-Ryu

Rating: mature
Tags: Alternate Universe, Anthro, Comedy
Length: 3347

Basically a bunch of very busty anthro mares oil wrestling that also involves tentacles

A monthly event known as the Stamina Championship is set up by Cheerilee. The rules are simple – if a contestant orgasms or is pushed off the side, they lose, and are eliminated.

However, there is one catch – the large, lubed mat any oil wrestling match takes place on is, in the Championship, surrounded by a waist-deep moat, filled with oil and magic-generated tentacles! And whenever a contestant orgasms, they are pulled into the tentacles for a thorough fucking.

Whichever mare is left standing (or indeed kneeling, or lying, or basically in any way they're not in the tentacles) wins! Who shall claim the… undisclosed prize?!

[size=1.5em]WILL CONTAIN:[/size]

[spoiler]Anthro (so don't fucking complain), huge breasts, even huger breasts, oil wrestling, squirting orgasms, tentacles, sex, lube, more lube, rampant lesbian sex, tentacles, lactation, breast milking (seriously there's a lot) and even more tentacles. Also I think there's going to be a changeling in here somewhere[/spoiler]

there are a lot more characters in this than the tagging system allows

Published 1970-01-01 00:00:00 UTC
Last updated 2015-04-21 01:10:01 UTC

Chapter 1: Pegasus Match

Today, on one of the many beaches on the West Coast of Equestria, there was a sizable yet not overwhelming crowd gathered - and what they had come to see was well worth watching. A large, 15x15 ft., lubed-up padded mat had been set up on the beach and partway buried in the sand. It would have seemed like a typical erotic wrestling match, if it weren't for the mostly-Wonderbolt contestant list and the peculiar moat surrounding the mat.

Yes, this moat had been dug out, lined with plastic sheets and filled with purple, lavender-scented oil. What purpose it served was unknown as of yet, but it was there nonetheless.

Cheerilee walked up to the edge of the mat, holding a microphone and clad in a two-piece green bikini, with a smile on her face.

"Mares and gentlecolts, welcome to the first match of the Stamina Championships! The rules are simple - orgasm, and the contestant is out. The same goes if they fall in the moat!" Cheerilee said, getting a good cheer out of the crowd.

"For the first match, the contestant list is suuuure looking good! First, we have the one-and-only.. Rainbow Dash!"

At that, the blue pegasus stepped out of the crowd, walking with a swing to her hips, making her curves jiggle as she walked, her wings folded onto her back. She only wore a black thong, her double-G-cup, huge breasts wobbling and jiggling with milk as she made her way to the edge of the mat. Her pink eyes sparkled with determination and self-assuredness.

She made sure to pose for the crowd, cupping her breasts and winking, stretching those wings out, which got a roaring applause for the steadily-growing crowd, as well as a few camera flashes. "That's right, folks - and I think it's safe to say that I wanna cum inside Rainbow Dash," Cheerilee joked, which got a smattering of laughter from the assembled ponies. Dash took no offense - it was a running gag anyway.

"Next, we got the Wonderbolt leader, so give it up for CAPTAIN SPITFIRE~!!"

Spitfire simply flew down from above, clad in a blue and yellow Wonderbolt bikini, her FF-cups displayed nicely along with her toned, yet curvy body, the bikini bottoms clinging to her camel toe. The crowd gave a similarly roaring applause for her, with even a few whistles here and there as she took her place next to Dash.

Cheerilee gave a mock salute to Spitfire before continuing, a grin on her face. "And so next, it's the Wonderbolt second-in-command, a recent stallion-turned-mare, Lieutenant Soarin!" At that, Soarin showed up from the crowd, wearing a red sling bikini - she'd paid good money for the gender-swap spell a while ago, and intended to take the cash prize for herself. She took her position next to Spitfire.

Dash leaned over to Soarin while Cheerilee was introducing Derpy. "Hey, Soarin," she whispered. "I hear there's gonna be tentacles," Dash then grinned, amused at Soarin's fear of tentacles, evidenced by her scared look and her wings, tightly folded down onto her back. "Shut up, Dash." Spitfire sighed. "Lieutenant, ignore her - there probably won't be tentacles, she's just trying to scare ya," she reassured her second-in-command.

Derpy then joined the line-up, wearing a yellow two-piece, approaching in a bubbly, cheerful manner. "Hey girls!" she beamed, her G-cup breasts jiggling as she leapt up onto the platform they were all standing on.

"Oh, hi, Derpy. Didn't expect to see ya here today," Dash smiled, making room for the wall-eyed mailmare.

"Oh, well, I'm in the wrestling club - thought I might as well try out against Wonderbolts," she shrugged happily, waving to the crowd.

"And finally, the newest gal on the block, fresh from Neighpon, Night Glider!" Cheerilee announced.

But there was no sign of her.

"Uh.. Night Glider? That's your cue," Cheerilee tried again, a nervous smile on her face.

Suddenly, a sonic boom rippled across the beach, and before anyone could figure out what was happening, Night Glider impacted the beach at an angle, skidding to a halt near the arena. She was wearing a black one-piece, with obviously recently-expanded FF-borderline G breasts stretching the latex, which made it cling to her labia and other curves. Night Glider gave a shallow bow and apologized.

"Gomen ne (apologies)," she said. "I'm a little late."

"Well, that's okay, Glider - better late than never, huh?" Cheerilee beamed, managing to diffuse the awkwardness. Night Glider stood on the platform with the others, her hands in front of her lap, her arms pushing up those tits. Suffice to say, RD was a little surprised Night Gilder would take breast enhancers so readily for a match - but it didn't seem to affect her already-supersonic speed in the slightest, and nor did Dash's own chestiness affect hers.

"So! Now that they're all here, lemme give you all the rundown," Cheerilee then said. She gestured to the pit around the arena mat. "That, people, is the dreaded Tentacle Moat of Doom!!" she proclaimed, just as a purple light filled the oil in there.

Princess Twilight gave Cheerilee a wink from inside the crowd. She was bikini-clad, too, but she was a spectator this time...

"Yes, it means that if a mare orgasms, she's subject to a bunch of tentacles' whim! That's the same if she's pushed out of the arena, too! Of course, it's all very safe, but even so, the losers are all eliminated from the match!" Cheerilee went on, seeing a little out of breath at this point, a little sweat dripping down her... it was a rather hot day, after all. At that, the contestants all entered the arena, the tentacles that filled the moat forming a very handy footbridge for the mares who walked over it. Dash flew over the moat and landed in a kneeling position, her legs spread wide, as if already teasing somepony.

Spitfire adopted a similar pose, as did Soarin. Night Glider, however, got down on one knee and put a hand on the lubed mat, struggling to keep her balance. Derpy, however, just sat down, smiling to herself.

"Are you ready?!"

The crowd roared with applause and cheering, ready to see some action.

"Then 3! 2! 1! GO!!"

Spitfire grinned widely as she slowly made her way towards Rainbow Dash, with Soarin in tow as she made her way towards her, not really paying Night Glider much attention.

Derpy seemed to just be watching with a goofy, innocent enough grin. As they began, six tentacles slowly rose out of the moat, each one was several inches thick, but had the odd smell of strawberries and dripped a pinkish goop off the tendrils as Spits launched herself at Dash, trying to grab at those big blue knockers, Soarin would try to grab that thong.

"We're gonna make you regret wearing just a thong!" She jeered as Spitfire's impact bowled Rainbow over, knocking her flat on her back before she could react. Spitfire then roughly groped and squeezed those big blue tits, using her wings to pin Dashie to the mat as she continued to have a go at those breasts as Soarin was having difficulty pulling Dash's thong off thanks to RD's struggling.

But they didn't count on Night Glider being nearby - she slid across on her knees and tackled Soarin, pulling her away from Dash. "And you're gonna regret wearing a stupid sling bikini!" she said, pulling the sling bikini off of Soarin's shoulders and shoving the Lieutenant's face into her tits, holding her there with her wings and one hand, and fingering that pussy with her other one.

"I got'cha covered, Dash!" Night yelled as she grappled with Soarin, who struggled against her hold, moans coming from her smothered mouth. It seemed Soarin was going to be the first to go, at this rate... Meanwhile, Derpy was still sitting over there, smiling innocently.. maybe that was her plan, to wait until whoever was left was tired out.

Dash was free to try and get Spitfire's bikini off, grabbing her top and ripping it away, but Spits was putting up a fight over the ownership of her bikini bottoms. Spitfire herself grabbed Dash by her shoulders and pinned the blue wonder onto her back, sliding down and forcing her into a kiss on the lips. She certainly enjoyed it, and judging by the crowd's reaction, everypony else did too. Their breasts mushroomed and squished together as she sucked on her tongue, her hands already working down that black thong.

Meanwhile, Soarin certainly wasn't expecting to be breast-smothered - she didn't know much about this Night Glider, only that the Captain had tried her out, but apparently it didn't go so well during the flight exam. Either way, her situation was going downhill as the red straps of her bikini were pulled aside to reveal a pair of double-F-cup breasts and her thick, dark and hard nipples. Being stuffed into the hot latex made it hard to concentrate, so she would try to grab her by her hair, which was much like Spitfire's own, and gave it a few hard yanks to try and pull her away.

Dash had half a mind to struggle and half a mind to relax into it - but her inherent competitive side prevailed, and Dash shot her hands down to Spitfire's bikini bottoms , pulling them up rather quickly then attempting to push her to the side - they were both rather close to the edge of the tentacle pit, as it was, and there were one or two tentacles already waving and undulating about.

Night Glider was trying her best to withstand the pain of having her mane yanked, but it proved too much, and so she resorted to turning around, then throwing Soarin behind her, on what looked like a collision course with Derpy. Derpy was sat there innocently, but as she saw Soarin sliding towards her, she beamed, shuffling to the side. When Soarin slowed down near her, Derpy placed her hands on Soarin and pushed her away rather hard, which made Soarin, struggling and trying to resist the low friction, slide towards the tentacles...

"Oh, this looks bad, folks - Soarin's gonna have a hard time getting back, and she's nearly at the tentacles!" Cheerilee commentated, the crowd's anticipation growing. Derpy sat back down, cross-legged, humming to herself while she calmly groped and squeezed her grey breast, a little milk trickling out of her nipple as she let out a relieved, happy sigh.

Spitfire groaned as she would sit up and pull away, revealing her own awesome orange breasts to the crowd, her nipples already hard. She gave them a quick show, along with Dashie, before sending them plummeting down towards her face, intent on smashing them against her and further smothering her...

Soarin, on the other hand, was skidding closer and closer, her wings extended out, causing the friction to increase. Her wings flapped hard as her legs hung slightly over the pit, but for the most part, she had caught herself from being eliminated first. The tentacles were seemingly slightly impatient, with one or two gently brushing against her legs as she pulled herself back into the ring. The only opposition left was Derpy, because Night Glider was intervening between Spitfire and Dash before the former KO-ed the latter - she had Spitfire by the waist and was trying to push her into the tentacle moat, but was being met with resistance from the Captain.

Derpy turned around and saw Soarin trying to get back up. She called upon all her wrestling club experience, ready to finish her off...

But just ended up sitting on top of Soarin instead, who was no closer to being eliminated. Derpy was simply sat on top of Soarin's back, smiling happily and innocently, while Soarin was dumbfounded and mildly confused as to what kind of wrestling experience Derpy was meant to have.

Meanwhile, Spitfire had been grappled by Night, held on her back while Dashie made a show of licking Spits out. The crowd was on the verge of thunderous applause.

"Ready to cum, Captain?" Night Glider teased her while Dashie slurped and lapped deeply at Spits' pussy, her muzzle and Spits' thighs soaked with pussy juice - and the Captain was quite close to an orgasm, but couldn't do much about it as Night was pinning her down, and she was rather heavy at that. Meanwhile, Derpy was being rather helpful in sitting on Soarin - this way, Soarin couldn't help her Captain, and Derpy was very content to sit there rather comfortably, at least until Soarin decided to step up her game...

Soarin grunted as she was pinned down, gasping. Derpy may have been sitting on her back, but Soarin could feel something warm dripping down the side of her head - it was obvious Derpy was rather aroused by this. She squirmed beneath her, trying her best to try and get her off. "C'mon Derpy...you wanna be a friend and help me up?" she'd ask her, only getting a giggle and a shake of the head from Derpy.

At the same time, Spitfire was already in quite a bad situation, her pussy getting licked, slurped, and further eaten out, her legs writhed and gasped as she herself was about to ride out an orgasm, but she was very much ready to get the other two off, though she wasn't planning on her legs kicking and spasming so badly. A kick went straight to RD's chin more than likely stunning, but even possibly knocking her off the side...

"Ooh, what a hit! I'm sure that was accidental, but it looks like RD's got a one-way ticket to Tentacle-Town!" Cheerilee commentated, the crowd cheering on Spitfire.. and getting ready to bear witness to the first KO of the match.

Dash shook off the kick to the face, recovering from the shock, but she was kneeling right on the edge, and tried to steady herself. Alas, she fell backwards into the moat, making a splash of purple oil. As soon as she fell in, tentacles wrapped around her limbs, lifting her up a little way. Dash struggled a little bit, but to no avail as she was pulled down onto the surface of the oil, which felt slick and warm on her body.

A few tentacles slithered up her body, coiling around her breasts and squeezing rhythmically, latching on to her nipples by forming a suction cup shape, and another pushed up between her cleavage and its tip tried to get between her lips. Meanwhile, a few more were tending to her lower regions, pressing against her camel toe and pulling off her thong. Thick, lubed purple tentacles then pushed Dash's pussy and her ass, stretching both her wet, lubed waiting holes then slowly pistoning in and out, getting muffled moans of pleasure from her, since one tentacle was in her mouth, its secretions tasting like fruit and lubing her up nicely. She was being milked as well, with creamy, rich milk being sucked from her breasts like a milking machine. As per the rules, she was to be in that pit until the match ended.

Meanwhile in the ring, however, Night Glider still had Spitfire pinned down, and just needed a little more to send the Captain over the edge of orgasm, so she began rubbing her crotch against Spits', sure that it would work...

Derpy was still sitting on Soarin, but she then put her legs either side of Soarin's head and pushed, sending Soarin sliding backwards into the tentacle moat. Derpy got off just in time, going back to sitting on the mat with a smile, her bikini bottoms seeming rather wet with her arousal.

Spitfire groaned and moaned loudly as she felt her continue to grind against Night Glider hard, she bit her lip and looked up at her, trying to grab and pull her into a kiss, though it seems as if she was going to be the second eliminated... or the third...

As Soarin got kicked by Derpy, the poor Wonderbolt subordinate skidded towards the edge, and promptly fell into the moat to the side, looking around in fright as she felt a pair of tentacles grab her legs, grunting as she was pulled up and held hanging upside down, just as a separate pair of tentacles would plant themselves directly onto her breasts, latching on as they began to suck out her milk. "Ohh! W-why did I get that magic lactation treatment~?!"

"Ooh, and that's Soarin in the pit! Hope she at least enjoys herself.." Cheerilee said as another tentacle began pressing itself against Soarin's labia. Dashie was being milked and fucked as well, her legs spread wide as she was vigorously tentacled - those in the pit were, as per the rules, in there for the rest of the match.

Meanwhile, Night Glider, Spits and Derpy were all that remained. Derpy was sat in her usual place, humming happily and enjoying the midday sun while Night and Spitfire grappled and grinded pussies. However, it seemed that Spits had better control than Night did, as the dark blue pegasus let out a moan as she orgasmed, soaking her swimsuit. She only realized her mistake as tentacles came slithering towards her and wrapped around her wings, arms and legs and soft, squishy breasts, then began dragging her into the pit.

"Oh my, it looks like Night Glider's out as well! Only Derpy and Captain Spitfire left, folks - let's see who comes out on top!" Cheerilee shouted, the crowd cheering on both Derpy and Spitfire.

Now that Spitfire wasn't being grappled anymore, she could now pay her full attention to Derpy. Spitfire stood up, stretching as she would gaze at the mare who she figured would have gotten eliminated at the start. Spits took in the mare who seemed to be already dripping pre-juices and was topless as well. She then took careful steps towards her.

"Uh..did you take out Soarin'?" she asked her. The Pegasus took in Derpy, it looked as though she hadn't broken a sweat whereas she was stuck there, nude and already dripping all over her thighs.

Derpy just smiled and looked around at the three mares in the tentacles - Dash was orgasming one after the other, being pumped full of the tentacles' secretions, on top of being milked, Soarin was being given the same treatment - and meanwhile, Night's swimsuit was proving to be quite an obstacle for the tentacles, though she was still bound up and sucking on a tentacle. "Yep! I just sat down on her the whole time," Derpy beamed, only wearing her bikini bottoms now as she stood up. "Bring it on!" she smiled, bracing herself.

Spitfire spread her large, yellow wings and steadied herself before moving towards her and grabbed her, pulling her into a kiss, intent on holding her there and making sure she'd stay there to enjoy it. She made out with her as she would then reach up and cup those grey breasts, her thumbs rubbing those fat nipples, rubbing and pressing against them.

"Listen Derpy, if you... let me win, I don't want to get too rough with ya - I'll let you be an honorary 'Bolt staff member~"

"Y--You will?" Derpy asked, all but stunned for just a second as she pulled away to speak, despite Spitfire holding her close.

"Um... no! I don't wanna--"

Derpy was cut off by Spitfire tripping her up, making Derpy land on the mat at the Wonderbolt Captain's feet. Spitfire then simply pushed her into the tentacle moat, where the purple tentacles rose up and grabbed hold of her, signalling the end of the match.

And not even a few seconds later, Derpy came to an orgasm, at which point the purple tentacles held the pegasus upside-down.

"And there we have it! Captain Spitfire wins!" Cheerilee said into the mic as the crowd erupted with cheering for the Wonderbolt.